


The Romantic Awakening of Dean Winchester

by MyShipWillNeverSink



Category: Supernatural
Genre: Alternate Universe - College/University, Blow Jobs, Dirty Talk, Experienced Castiel, Light Angst, M/M, Nervous Dean, Recreational Drug Use, Second-Hand Embarrassment, Shotgunning, Work In Progress, sort of
Language: English
Status: In-Progress
Published: 2017-02-09
Updated: 2017-05-25
Packaged: 2018-09-23 02:23:31
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 5
Words: 12,858
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9636653
Author URL: https://archiveofourown.org/users/MyShipWillNeverSink/pseuds/MyShipWillNeverSink
Summary: Dean wonders if maybe he's not as straight as he's always assumed, and decides to explore his options. Meg has the perfect candidate to help him out.





	1. Taking My Chances

**Author's Note:**

> This idea came to me because I want more fics with less than traditional sex scenes. Sometimes sex is awkward, you know? But there's also Dean's discovery of the difference between romantic and sexual attraction that I'll be exploring later on - fun stuff! 
> 
> I'll update the tags/rating as I add chapters - I already have two completed and they're being written fairly quickly, so I doubt I'll abandon this story.

Charlie coughs and waves a hand in front of her face as Meg takes a long drag of her cigarette and blows smoke into the air, the wind taking it in Charlie's general direction. Meg shrugs apologetically and flicks her ashes off the side of the porch. 

"I wish you wouldn't do that," Dean sighs from where he's laying on the wooden floor, hands linked behind his head. 

"You used to smoke," Meg points out, taking another drag. "If we're all going to die, I might as well enjoy the time I have now."

Charlie rolls her eyes. "That is such bullshit, and you know it." They fall silent, listening to the steady spring rain pour down, feeding the long-dead grass and plants that haven't quite recovered from winter. 

It's a Saturday afternoon, and they’re taking advantage of their first day of spring break. None of them have any real plans to go anywhere, so they've opted to not leave their rented house off campus in order to vegetate and recover from midterms. Meg and Charlie had been random roommates their freshman year in the dorms and had grown close enough to figure there was no need to stop being roommates for the duration of their undergrad. Dean’s been best friends with Charlie since middle school, so renting with them seemed like the natural thing to do. His father finds it strange, but he doesn’t really care what the old man thinks, anyway. 

"Where the hell is Benny?" Dean asks lazily, eyes closed and right shoe tapping a melody into the side of the house. 

"Probably with Andrea. I expect we won't be seeing them for a while, honestly," Meg says, finally putting her cigarette out in the ashtray next to her knee. 

Charlie snickers. "It's about time, honestly. They've been dancing around each other for months." They fall silent again and Dean smiles. This is what he loves about his eclectic group of friends; they understand the importance of being quiet, of sitting down and listening to the first warm rain after months of ice and snow. 

"What about you, Dean?" Charlie asks. "Have you thought about seeing anybody?" 

Of course, sometimes they have to ruin the perfectly good silence. 

Dean opens his eyes and sits up, running a hand through his hair in frustration. "I don't know, Charlie. I thought about picking someone up last night, but... I haven't been having the best luck with women. One minute, everything seems fine, and the next, I can't... feel anything anymore. Maybe I'm just broken. It happens." 

Meg scoffs. "You're not broken, dumbass. Have you considered that maybe you just aren't romantically attracted to women?" 

Squinting, Dean holds a hand up in confusion. "Not romantically... what? That doesn't even make sense. Of course I like women." 

Now that he thinks about it, however, that does make some sense. He's never been interested much in the feelings part of a relationship. In fact, he's treated most of his girlfriends like... well, like friends with benefits. It's why they never worked. 

"Dean, romantic attraction is different from sexual attraction. They don't always match. Didn't you go to that Spectrum meeting?" Spectrum is the LGBTQ social organization on campus. He must have missed that particular meeting, or just hadn't been paying attention. He goes to those meetings for Charlie, to be a good ally. Now he feels like a dick for not paying attention. The guilt is apparent on his face, and Charlie groans. "I don't even know why you go if you aren't interested in the educational stuff."

"I think it's interesting! I must have had a lot on my mind that night or something. Anyways, so what are you saying?" 

Meg shrugs, flicking her lighter on and off. "Maybe you're aromantic. Maybe you're homoromantic. Have you ever experimented with guys?" 

Now it's Dean's turn to scoff. "No, Meg, I haven't."

"Why?"

That... is an excellent question. Why hadn't Dean ever experimented? Probably because he never really had a problem finding women who were willing to try him out. They may not ever work out, but while it’s happening he's not really thinking about the possibility of being into more than one gender. So Dean looks up and glances and both of his best friends and shrugs. "I honestly just never thought about it. You think I should?" 

"It can't hurt," Charlie says, grinning. "Ooh, this could be fun. I always thought you were straight as a sewing needle. How are we gonna do this? I don't know very many guys who aren't straight and would be willing to just be your experiment." 

"I don't even understand what we would be experimenting. How am I supposed to know how to differentiate between romantic and sexual feelings? What if it's the opposite for guys and I can only be romantically attracted to them?"

Meg leans over and awkwardly pats his bicep. "Dude, it'll be fine. This is just a... trial, of sorts. And I actually think I know who'd be willing to do this with you. You'd be in good hands." 

Dean looks away, not knowing whether or not this is something he’d want to do. The rain slows to barely a sprinkle, the sun starting to shine through the thinning clouds. They watch a squirrel dart up a tree and Charlie clears her throat. "Who do you have in mind? Someone we know?" 

"Clarence. Well, okay, his name is Cas, but I call him Clarence to fuck with him. He's in my major and he's the only person I can stand - philosophy majors can be pricks."

Dean narrows his eyes. "What the hell makes you think he'd want to... to --" 

"To be your sexual experiment?" Meg shrugs nonchalantly. "He's a chill dude. He invited me to an orgy once." 

"An orgy?!" Dean squeaks, pulling his knees to his chest protectively. 

Both of the girls laugh, and Meg lights up another cigarette. "Don't worry about it, hot stuff, you won't have to participate in an orgy if you don't want to. Cas is just... sexually liberated, I'd say, and probably would be okay with being your sex toy. I can ask him, if you want. I think he's staying in town over break." 

A fly makes its way into Dean's personal space and he swats at it, grumbling. "I'd like to meet him or something first. I don't know. Why don't we invite him over?" 

Charlie's grin turns positively evil and she brings her hands in front of her, rubbing the palms together. "Maybe we should smoke and have a game night. Nothing like a good high and Diddy Kong Racing to get everyone comfortable." 

~

It's confirmed no less than two hours later that Cas would be coming over that evening for game night. He even said he'd bring his own weed, which Dean finds weirdly considerate. 

The whole deal is weird, honestly. Meg swears she didn't say anything to Cas about what Dean’s intentions might be, but Meg tends to bend the truth so he can’t be too sure. Maybe Dean will meet Cas and won't be attracted to him, which would certainly make things a little simpler. 

Now that he’s thinking about it, he's never by any means been _repulsed_ by men. He's seen gay characters on tv and in movies and it's not like he thought _ew, how do they do that?_ like he’s seen in other male friends throughout the years. He's just never really given it a lot of thought. And now that he is, he feels like a fish out of water, completely out of his element. 

“Quit fidgeting, you're making _me_ nervous,” Charlie's says from the couch. She's using a toothpick to clean out her elephant-shaped bowl, eyes narrowed in concentration. 

“When is he supp --” Dean is cut off by the doorbell ringing. 

Meg saunters in from the kitchen. “Don't worry, I got it,” she says drily, and opens the door. She smiles. “Clarence! Welcome to my humble abode, I hope everything here is to your liking tonight.” She sends a wink Dean’s way and his face flushes a bright red. Damn it. 

It flushes even deeper when Cas comes through the door, all six feet of him donned in different shades of black. His jeans are jet black and form-fitting, his t-shirt is a charcoal black, as are the aviators over his eyes. He has his hands in his pockets, looking relaxed. 

Cas flips his sunglasses onto his head and glances at both Charlie and Dean, the former of which is trying to hold back a laugh at the shocked look on Dean’s face. “You both know my name isn't Clarence, right?” He sounds like he could easily voice act a car engine. _Shit_. 

Charlie sets her bowl on the table and stands up, wiping her hands on her jeans before bringing one up with a wave. “Yeah, it’s Cas, right? I'm Charlie. This is Dean.” 

Dean gives a pathetic, withering smile when Cas looks back at Dean and he catches Meg looking at him with an eyebrow raised. 

“Dean,” Meg says, eyebrow still cocked, “will you help me in the kitchen real quick? I need your height.” Dean jumps up from his place on the floor and makes his way to the kitchen, avoiding eye contact with Cas, who is now staring at him intently. 

Once in the kitchen, Meg bursts out laughing. “Dean, haven't you ever heard of a poker face? I mean, Jesus, you might as well have asked him to take off his pants right then and there.”

Dean gapes at her and whispers, “Oh my god, keep your voice down! What are you talking about?” 

Naturally, Meg doesn't answer the question directly. “Oh, I just _knew_ Cas was the right one for this. I mean, he's made of sex appeal. This is _hilarious_.” 

Dean grits his teeth and resists the urge to pull his hair out. “He's attractive, so what? I was surprised. You never said what he looks like.” 

“Thank god I didn't, it was so worth it to see the look of pure lust and surprise on your face.” 

“How is that even possible? I've never looked at a guy like that before. I've never found a guy anything more than aesthetically pleasing.” 

Meg tsks and leans against the counter. “You've never actively looked before. Never really allowed yourself to believe in the possibility that, hey, you might want to see a dick that isn't yours.” Dean rolls his eyes and Meg just keeps going. “The genitals want what they want, Dean, and yours want Cas.”

“Pardon?”

Dean and Meg whip their heads around to find Cas standing in the doorway, arms crossed and bicep leaning on the frame. Meg whispers _oh, shit_ before laughing so hard she has to grab the table for stability and Dean puts his hands to his face and wishes death would be swift and merciful.

Dean looks up through his fingers at Cas and is relieved to see him smiling. His face is lit up by it, his bright blue eyes twinkling, and yeah, he might be laughing at Dean, but it's better than seeing anger or discomfort on his face. Dean drags his hands down his cheeks and sighs. 

“Let’s pretend that didn't happen. What kind of pizza do you like? We've got a lot of frozen pizzas to choose from.” Dean turns towards the freezer and prays to whoever is listening that Cas lets it go. 

Mercifully, he does. “Anything but mushrooms.” 

Dean looks over his shoulder and raises his eyebrows. “Even pineapple?”

If Dean didn’t have his face buried in the freezer, he probably could hear Cas approaching. He doesn’t, so when Cas says, “Never had it, but I like to try new things,” right next to his ear, he gives a very undignified squeak of surprise. Dean closes his eyes and rests his forehead on the edge of the fridge door, considering closing the freezer door on his head to put himself out of his misery. 

Cas laughs and rests his hip against the counter. “Okay, I think you’ve been embarrassed enough for the evening. I’ll take pepperoni.” 

Nodding, Dean takes out a pepperoni and a cheese. “Meg, what do you --” He cuts off as he turns around and realizes she’s not in the kitchen anymore. It’s just Dean and Cas, which makes Dean’s face heat up once again. Dammit, he’s not usually this much of a complete jackass. He thinks it might have something to do with how infuriatingly _calm_ Cas seems. 

“So,” Cas says, “what’s your major?” 

“Mythology and Latin.” He looks over to see Cas grinning at him and chooses not to have the discussion his majors usually elicit. “You’re philosophy, right? Meg said you’re in her classes.” 

“Yes. You’ll soon see how fun it is two get high with two philosophy majors - give us an hour to start talking about the meaning of life.” 

Dean groans and slides the pizzas onto the pizza pans. “Don’t even get me started, Meg pulls that shit all the time.” He turns back to Cas. “What’s Cas short for?” 

“Castiel. I know, it’s weird, my parents like being eccentric.” 

Dean purses his lips. “Castiel,” he says, sounding out each syllable slowly. “I like it.” 

A loud thump comes from the living room and they both crane their necks to listen to the ruckus. A faint, “Charlie, you always get to be Conker!” can be heard, and Dean chuckles. 

Cas raises an eyebrow. “Conker?” 

“Yeah, the squirrel. From Diddy Kong Racing? Have you never played it?” The oven beeps, indicating it’s preheated, and Dean slides the pizzas in. 

Castiel shakes his head. “Um, no.” 

“Well, what the hell are we still doing in here?” 

~

Turns out, Cas is a natural at Diddy Kong Racing. 

This infuriates Dean, because it’s not fair at all for someone to be blessed with sex appeal, a sense of humor, _and_ a blind talent for video games. 

Charlie tosses her controller down as Cas wins yet another race. “Maybe you should come over and just beat all of the regular levels for us.” 

“Yeah,” Dean stretches out the word like it’s made of melted cheese. He takes another hit from the elephant bowl and sits back against the couch, his head to the right of Castiel’s knee. “Maybe he can finally get me past Snowflake Mountain.” Dean gently nudges Cas’s shin with his shoulder and Cas pushes back. 

“I think you need to pass me that.” Cas reaches for the bowl and Dean hands it over, smiling. Cas scoots forward and lowers himself off the couch so he’s sitting next to Dean. Meg takes the controller Castiel had been using and moves over to wear Charlie is sitting directly in front of the TV, giving Dean and Cas more space. It would have made Dean nervous, if he were capable of feeling nervous anymore. 

“So, Dean,” Cas starts after taking a hit from the bowl, “what exactly was Meg talking about earlier, in the kitchen?” 

Dean blushes, but continues smiling and leans his head back against the couch cushion. At this point in time, he sees no reason to be anything other than honest, so that’s what he does. “I’m having a bit of a sexuality… crisis? It’s not really a crisis though, like I’m not upset about it. I just don’t know what I want, and I’m trying to figure it out.” Dean’s head lolls to the side and he looks Cas in the eyes. “I’ve never tried anything with a guy before, but the idea doesn’t necessarily put me off. It’s not something I’ve really ever considered doing until today.” 

Cas takes all of this information in with narrowed eyes, lips pursed in thought. He looks at Dean, glances quickly down to his mouth and back up. It was fast, but Dean notices. Cas licks his lips. “I see. So you want to see if… it’s possible, for you to be attracted to men as well as women.” 

“Yes!” Dean says, pleased. “I never really thought about it, but I’m not really… romantically attracted to women, I guess. Just sexually. I want to see if it’s the same or different with guys.” 

Cas nods. “Well. I’m good at experiments. I have a small one, if you’d like to try it out?” Dean glances over at the girls, still engrossed in the game and yelling in excitement. Cas laughs softly. “Don’t worry, it’s not obscene. Just something small. Have you ever shotgunned before?” 

Dean knows what it is, but hasn’t done it before; he shakes his head. Cas grabs the bowl and lighter again and takes a hit, keeping his eyes on Dean and shuffling closer when he takes the bowl away from his mouth. Dean exhales and leans into the other man’s space, feeling electrified. Cas opens his mouth and slots it onto Dean’s, gently, and exhales. Dean breathes in the smoke, lips tingling and eyes closing. When it’s over and Cas is closing his mouth, Dean leans in and turns it into an actual kiss, quick but obviously on purpose. Cas smirks. 

“I think you have your answer, Dean.” 

Quickly, Dean leans back and looks down at the carpet. That feels like he’s saying, “we should stop doing whatever we’re doing,” but when he looks back up at Castiel it’s to an expression that’s anything but unaffected. Cas’s pupils are dilated and he’s gazing at Dean’s mouth. 

“Maybe, uh,” Dean swallows to try to moisten his extremely dry mouth, “maybe I need further… proof.” 

Cas grins and leans in close to Dean, his breath on Dean’s cheek positively intoxicating and he closes his eyes. Before they can seal the deal, however, Charlie coughs loudly from right beside Dean. 

“I don’t mean to break this up but it looks like whatever is starting here shouldn’t be finished with company present, and I also want my bowl back.” Charlie is smirking as Cas hands the bowl over and Dean shakes his head, glaring up at Charlie. 

“Okay, then. We’ll just, ah,” Dean stands and holds a hand out for Cas to take, which he does. He keeps his eyes on Cas as he continues, “finish this elsewhere?” 

He nods and as Dean is leading him quickly to the hallway towards his bedroom, Cas waves at the girls. “Feel free to smoke my stuff, it’s in my coat pocket.” Meg gives a triumphant, “Woop!” and then they’re in Dean’s room and the door is closed and Cas is pushing Dean against the wall. Dean’s head spins and he closes his eyes, breathing heavily.

If you had asked Dean a day ago whether or not he’d be potentially having sex with a man the next evening, he would have been both bewildered and confused. Now, he’s wondering how he didn’t think to try this before. Better late than never, right?


	2. The Night Ain't Over

**Notes for the Chapter:**

> So, this is my first time writing/posting any explicit content and I would DEEPLY appreciate any and all feedback. If something sounds out of place or patchy, let me know so I can correct it and make it better for future readers. 
> 
> Also, this fic is un-beta'd, so any mistakes are my own and I'll gladly fix any that are pointed out to me!

“Dean,” Cas says, his gruff voice pitched lower than should be possible, “you don’t have to do anything you don’t want to.” 

The sound of his voice makes Dean go a little weak at the knees, but he meets Cas’s gaze steadily. “Nah, I want to. No harm in trying, way I see it. Meg said I’d be in good hands anyway, so really I --” Cas cuts him off by putting a hand on his jaw and bringing his lips forward for a searing kiss. A small noise makes its way out of Dean’s throat and the sound is lost in the kiss between the two men. 

As far as not knowing how he'd react, Dean can now officially say his sexual appetite at least includes this one man. It's new and confusing and he's trying not to think about it as Cas slides the tip of his tongue across Dean’s lower lip. He opens his mouth and their tongues collide, wet and messy and _good_.

Dean pushes against Cas and guides him towards the bed, where they fall in a tangle of limbs. It might be the high, or the feeling of doing something he's never done before, but now is when Dean starts to feel excessively nervous about the whole ordeal. Cas feels him tense up, and pulls back. 

“What do you need me to do to make this more comfortable?” Cas asks, face open and honest. It's refreshing; the few times Dean has had sex before, it was all movement and feeling and no talk. He needs to talk himself through it. 

“I don't know what I'm doing. It might help if you… talked me through it? I'm sorry, that's embarrassing.”

Cas smiles and pats Dean’s hand. “It's not embarrassing, it's fine. Sex doesn't have to be quiet and romantic and all about touch every time, you know.” 

“You seriously don't mind having to talk me through sex?”

Cas shrugs. “Why should I care? I think you're hot and it's cute that you're so flustered. Telling a partner what to do is a pretty huge turn-on for a lot of people, Dean.” 

The turn-on for Dean right now is Cas’s voice, so it seems like a win-win scenario. Dean just nods and runs his tongue on his bottom lip. Cas drops his eyes to follow the movement, and leans in to pull Dean’s lower lip with his teeth. He groans and Cas shifts to push Dean onto his back and continues the kiss, which Dean is sure is one of the best ones he’s ever had in his life. He’s so caught up in the sensations he doesn’t realize that Cas’s hands are roaming and it comes as a surprise when he brings a hand down to Dean’s inner thigh and squeezes. 

Dean yelps and his leg moves instinctively, bending at the knee and flying upward. Right onto Cas’s balls. 

Cas immediately rolls off of him and curls up, gasping in pain. Dean may still be high, but he recognizes quickly that he has royally fucked up and he tries to push the embarrassment aside to help Cas out. 

“Oh my god, I'm so sorry. I'm so stupid. I'll be right back.” Dean hops up and takes another look at Cas’s pained expression before running out of his bedroom and towards the kitchen. 

Standing beside the fridge, because Dean can never catch a fucking break, are Charlie and Meg. Meg takes one look at the panic on Dean’s face and raises an eyebrow. “Trouble in paradise? Figured you'd be in an orgasmic bliss by now.” 

“Can it, Meg,” Dean mumbles and opens the freezer to take out an ice pack. He reaches behind Charlie to grab a hand towel from the stove handle and wraps it. 

Charlie’s eyes widen. “Shit, Dean, what did you do? I'm guessing from the look on your face that this isn't just an experiment in ice play.” 

Dean grimaces and says nothing, opting instead to leave them hanging and hurrying back to his room. Thankfully, they choose not to follow. Cas is still curled up when he gets back to him, but the look of anguish on his face has mellowed out a bit. 

“Here, man,” Dean says, handing over the ice pack. Cas takes it and places it over the crotch of his jeans, and then starts laughing. Mouth twitching with the threat of a smile, Dean sits next to him and rests his head on the headboard. “This is so not funny.”

“On the contrary, Dean, this is absolutely hilarious. I've had some unfortunate things happen while in bed with someone, but this really takes the cake.” 

Dean closes his eyes and groans in frustration. “I get it if you'd like to, you know, leave now.”

The bed rustles beside Dean and he opens his eyes to see Cas setting the ice pack aside and turning to face Dean. “I'm not _that_ injured, Dean.” He runs his fingers down Dean’s spine, reaching under the hem of his t-shirt and splaying his hand over Dean’s lower back. He shivers; he's still really embarrassed but there's no way to not be affected by Cas’s hands. “I'll leave if you want me to, just say the word, but I personally think it would be more fun if I stayed.” The tips of his fingers barely brush past the waistband of Dean’s jeans and boxers and Dean’s breath catches and he leans forward as if to give Cas better access. 

“I think,” Dean's says, breathing choppy, “I would definitely like for you to stay.” Cas grins and uses the hand not currently in Dean’s pants to pull him in for a kiss. He runs his lips from Dean’s mouth to his cheekbones and up to his ear. 

“‘Hey girl hold me tight, the night ain’t over,’” Cas whisper-sings into Dean’s ear, clearly on the verge of laughter again. 

Dean chuckles and pulls back, eyebrows raised incredulously. “The Outfield? Really? Right now?”

“If you,” Cas pauses to nibble at his earlobe, “are dissing my favorite band right now,” and again to lick his way to Dean’s collarbone, “I'm going to have to reconsider this whole thing.” 

“No, ah, dissing here,” Dean gasps as Cas moves to unbutton his jeans. “I'm a little surprised your favorite band is 80s pop, but hey, it is what it is.” The last half of that sentence comes out shaky because Cas leans back to pull his shirt off, exposing a lithe runner’s body that makes Dean’s mouth dry. He reaches forward to rest his hand on Cas’s chest, marveling at how different it is from a woman’s body yet somehow just as satisfying. 

The funny thing (besides everything mortifying that has happened to Dean thus far) is that this was so unprecedented. Twenty-four hours previously he'd been considering going out to a bar and bringing a local girl home for a harmless fuck and now he's experimenting with a guy who is making him more worked up than he's felt since he was a teenager. Life is so goddamn weird. 

Dean looks up and sees Cas looking at him expectantly. “Uh, did you say something?” 

“What did you think my taste in music would be like?” 

The urge to roll his eyes is strong, but he holds back. “I don’t know, man, like Arctic Monkeys or some shit. If I knew you liked 80s music, I would have assumed Joan Jett or something, I don’t know.” 

Cas tilts his head to the side. “Why those two bands?” 

“They've both got kind of a sexy sound, and you've got the whole confidence thing down,” Dean shrugs. Why they're continuing to talk about this, he has no idea, but it's - oddly enough - not weird. 

A grin like a Cheshire Cat breaks across Cas’s face and he leans in. “So what you're saying is, you think I'm sexy.” His voice pitches low and Dean has to get a handle on his body temperature before he bursts into flame. 

“C’mon, man, that goes without saying.” The darkness is suddenly a very good thing because Dean doesn't want Cas to see the blush in his cheeks at the admission. Cas, either not catching Dean’s embarrassment or choosing to ignore it, leans in as if he's going to kiss Dean and holds it there, the space between their lips seeming to spark with electric anticipation. Dean leans in to close the distance but stops when a hand pushes on his chest. 

“We need to talk about boundaries while we’re not in the heat of the moment.” Before Dean can respond, Cas smirks and says, “And no, that was not an invitation to sing Asia to me.” 

Groaning, Dean flops backwards onto the pillows and crosses his arms over his chest. “You’re killing me.”

“I'm glad you're eager, but I’d rather be teasing you now than crossing a boundary and making you uncomfortable later.” 

That makes Dean pause and take a closer look at the man in front of him, whose shirt is off and eyes are sincere for some reason makes Dean feel like 14-year-old having his first make out session. He'd obviously been with a few girls, but no one had ever talked boundaries. No one really cared enough to do so. 

Not that he's thinking Cas cares about him deeply or anything, but to have someone care enough to not want to even potentially make him uncomfortable, well, that made Dean feel something. He didn't know what and he wasn't going to analyze it at the moment because they have boundaries to discuss. 

“Well, uh,” Dean brings his legs in and crosses them, resting his hands in his lap, “I would rather not, um. Have anything up my ass?” 

“That's completely fair. Anything else?” 

“I guess I'd rather not put anything up your ass either. Other than that, I'm not much of a masochist but a little pain is okay.” 

Cas’s eyebrows fly upwards and Dean almost wishes he could take those words back. Almost. “Okay. Pain how? Like choking or spanking or nipple play or -”

“Just nipples, that's fine,” Dean interrupts, his voice embarrassingly high with tension. He could feel himself getting hard again just from Cas describing thing matter-of-factly. Jesus. 

“Okay,” Cas says, running his hands up Dean’s denim-clad thighs. He's really wishing they'd gotten to the pants removal before having this sexual heart-to-heart. 

“What about you,” Dean says quickly, grabbing at the hands coasting toward his zipper and twining their fingers together, “what are your boundaries?”

Cas blinks and tilts his head. “I don't really have many, but for now let's just say my boundaries are the same as the ones you've named. Except I don't mind being choked, but if you haven't done so before I would recommend reading up on proper techniques before doing that one.” 

Dean swallows audibly and nods. “Okay. Noted.” 

Satisfied, Cas moves forward into Dean’s space and latches his lips onto the space right above his collarbone, wrenching a breathy moan out of Dean. He moved down to Dean’s nipples, giving his undivided attention to each with both his mouth and his hand. He bites down with enough force to make Dean arch and gasp. Unable to take it anymore, Dean grabs ahold of Cas’s hair and gently pulls him up for a bruising kiss, all tongue and teeth and the exchange of breathless gasps from one mouth to the other. Cas is an amazing kisser, even with the chaos of this particular kiss, and when he bites Dean’s lower lip, Dean can't help the loud groan that escapes. 

“Shhh,” Cas says, smirking, “Keep that up and Meg will never let you live it down.” 

“Let’s not discuss Meg right now,” is his reply and he pulls the other man back in. He reaches for Cas’s jeans and works on the button and zipper. With Cas’s help, he gets his jeans off and before he can pull on the boxers, Cas takes his hand. 

“You wanted me to talk you through this, right? This is an exploration for you.”

Dean’s pupils dilate and he nods his head quickly. “Yeah, definitely, talk me through it.” By this point, he really doesn't need the added instruction, but he’ll gladly take it if it means basically listening to Cas talk dirty to him in that deep tone. The push of his erection on his jeans is getting to be too much, however, so he shucks his jeans off quickly before Cas starts. 

“Okay,” Cas says, voice breaking as he stares at the bulge of Dean through his briefs, a wet spot already forming where the head is. He takes a deep breath. “Go ahead and take off my boxers, however you feel like. Pay attention to your reaction when you see my dick - this is, after all, a test to see if you can be sexually attracted to men.” 

Dean does roll his eyes this time and gently pulls down the black boxer-briefs, biting his lip to hold back a groan when Cas’s leaking dick springs out from its confinements. Test over, he passed, 100%. 

“Good. Now, I'm assuming you've masturbated before, so this next part is pretty much like - _oh_ , yeah, exactly like that, Dean.” Cas’s ‘lesson’ is interrupted by Dean being a shining student and taking the initiative, wrapping a hand tightly around Cas and pumping up and down. Cas arches his back and fucks into Dean’s fist, making filthy noises that has Dean palming himself through his underwear. When he twists his hand on an upward pull, Cas gasps and clamps his hand down on the sheets. 

“Is this good?” 

Cas opens his eyes and stares at Dean, chest heaving with his breath. “Fuck. Yeah, Dean, it's good.” 

It isn't good enough for Dean, though. “Would it be better if I used my mouth?” Dean asks sweetly, knowing full well what the answer is. 

Cas closes his eyes again and nods. “I think that… would be much better.” 

Dean’s first blowjob is… messy. At first, he takes too much into his mouth and nearly chokes and Cas has to pull him back by his hair and say, “Just go a little at a time. Use your hand on the rest - yep, yeah, oh my god you've got it.” He sucks lightly at the tip and then pushes forward a little to run his tongue underneath and the moan Cas gives has Dean moaning along with him, the vibrations adding to the sensations for Castiel. Cas bends his knee and Dean finds himself subconsciously leaning to the side to rut against his shin. Cas takes notice and pulls him up. 

“You,” he says, breathing heavily, “are a natural. And I swear to god I'm not just saying that, Dean.” He pulls Dean in for a quick kiss and then flips them over so he’s on top. “Can I take this off?” he asks, gesturing to the underwear. Dean nods frantically. When they're both - finally - naked, Cas gazes at Dean’s body hungrily. “How are you feeling about this? Have you found your answer?” 

Dean reaches up to latch his arms around Cas’s middle and brings him flush against Dean, both of their cocks lining up perfectly and sliding together, making both of them groan. 

“Yeah, Cas, I think I have my answer. Please, we gotta stop this pausing and talking thing. I want you.”

That seems to be enough for Cas and he growls and surges forward to latch onto Dean’s neck, licking and biting and sucking until Dean is bucking his hips and causing friction between their touching cocks. Cas reaches down and takes them both in his hand and starts pumping his hand, making Dean keen with pleasure. They're both thrusting to get as much friction as they can but it isn't enough and Dean brings his hand down to join and _oh, that's it_. 

Dean uses his other hand to pull Cas back up for a kiss, which he has to break almost immediately when Cas’s other hand finds his right nipple and rolls it roughly with two fingertips. Between that and the new feeling of another man’s dick sliding against his own, he comes quickly with a stuttered moan. 

Cas, eyes wide and looking down at the streak of come now painting Dean’s stomach and both of their hands, groans and comes not long after. He collapses beside Dean and they both stare at the ceiling, breathing hard and blissed out. 

“That,” Dean starts, speech slurred, “was _so good_ , Cas.” He pauses, reliving what just happened and then he sits up quickly. “Wait, we didn't use any protection. I completely forgot because you aren't a girl and I -” 

“Dean,” Cas soothes, rubbing a hand down his back. “It's okay. I'm clean, I was actually just tested for everything last week. Are you?”

“Yeah. Yeah, I'm clean.” Crisis averted. Dean lays back down and rolls over to look at Cas. “Thanks.” 

Cas huffs a laugh. “Anytime, Dean.” He stares at Dean for a minute and then rolls over and stands up, stretching his arms and popping his back. He moves around the room and puts on each of his discarded articles of clothing. Dean reaches to his nightstand and turns on the lamp. He grabs a pen from inside the top drawer. 

“C’mere,” Dean says and beckons Cas over. He grabs the man’s arm and pulls it under the light before writing a number on the top of his hand. “That's my number. You can text me, if you want.” 

Cas grins and reaches forward to tangle his fingers in Dean’s hair, pulling back just slightly to angle Dean’s head for a quick but messy kiss. “I certainly will,” he says with a wink, and just like that, Cas turns and exits Dean’s bedroom, closing the door on his way out. 

Sighing, Dean falls back down onto his pillows and turns out the lamp. What just happened? Amazing. Phenomenal. It hadn't even lasted long, but Dean had been so _into it_. 

Now he has his answer. He's definitely capable of being sexually attracted to men. Satisfied, he locks his hands behind his head and sighs happily. And Cas has his number. Maybe he would want to do some more… experimenting. 

Under all of this satisfaction is a strange and unprecedented feeling of emptiness. He doesn't touch the feeling, letting it brew under the surface without giving it the space it needs to breathe. If he were to analyze it, he might find that he's disappointed that Cas didn't stay. That they didn't talk more, touch more. He falls asleep actively thinking about the possibility of next time.


	3. In Your Company

**Notes for the Chapter:**

> I didn't know if I was going to do any chapters in Cas's POV, but this seemed necessary. Also I'm writing this so much faster than I expected to, so yay!

The house is dark outside of Dean’s bedroom. Cas figures Meg and Charlie must have gone to sleep… or outside so as not to hear the two men having sex. He tiptoes through the living room, using his phone as a flashlight to find his jacket and his shoes. 

When he slips out the front door, he’s a little embarrassed to see the two women sitting on the edge of the porch, legs dangling from the side. They must have heard them after all. They both turn back to look at him and Charlie smiles. “You want to join us? It's nice out.”

And it is nice, if a little chilly, so Cas decides there's no harm in staying for a little while longer. He sits next to Meg, who offers him a cigarette. He takes it, muttering a thank you and vowing _this is the last one_. He’s been trying to quit for months, and has at least stopped buying them for himself. Baby steps. 

“So,” Meg drawls, “How’d it go, hot stuff?”

Cas grins. He knew this was coming. “I'm not one to kiss and tell.” 

Meg slaps his arm. “Bullshit! Yes, you are.” Charlie giggles and leans around Meg to look at Castiel. 

“We’ll ask Dean for his details later, but what did you think of Dean?”

What _did_ he think of Dean? He's an anxious, funny, ridiculously attractive man. He had fun. “He's fun. He was really nervous, though, is he normally like that?” 

“No. Not even close; Dean is our resident playboy. His motto is usually ‘have sex first, ask questions later. Or never.’”

“Hmm.” He doesn't really know what to do with this information. And he’s trying not to dwell on it, but there's something that doesn't feel quite right in his gut. It probably has something to do with how quickly he left. “Does Dean normally have girls stay over when he picks them up?” 

Charlie gives a noncommittal sound. “Eh, it usually depends on how late they came home and how drunk they both are. No one has ever stayed past early morning, though. No romantic breakfast for two in this house.” Charlie glances at Meg. “At least, not for Dean.” Cas quirks an eyebrow and decides to ask about that later. 

Meg rolls her eyes and looks back to Cas. “Why, did he kick you out?” 

“No, I just left. But I didn't know if that was the right thing to do or not. I guess it was.” Cas looks down at his hands and scowls, trying to understand why he feels like he did something wrong. 

It's quiet for a few minutes, the only sound being the quiet chirp of the crickets in nearby bushes. It's cloudy, and the night seems to hover like a heavy blanket over the town. Cas decides he likes this area; the street is calm and dark, very much unlike his apartment on Riverside, next to all of the frat houses. It was fun his freshman year when he could show up at parties, but he longs for the quiet. He takes a long drag of the cigarette and takes his time blowing out the smoke. 

“Did you want to stay?”

Apparently, he's the only one who values silence. 

Castiel glances at Meg and sighs. “No. I don't know. If he had asked me to say, I probably would have.” 

Which is a terrifying thing for Cas to admit even to himself. He’s always been someone who’s unattached. A free bird. He looks down at the back of his left hand, which has Dean’s number scrawled on it. He already knows he's going to put it into his phone and text Dean before the weekend is over. 

~

[Cas: Hey, Dean.]

[Dean: cas! didn't know how soon I was gonna hear from you. wasn't expecting to only have to wait a day]

[Cas: Well, I had fun. :)]

[Dean: yeah? I was afraid I scared u off with my awkwardness and lack of experience]

[Cas: No, I thought it was hot. ;) Do you want to hang out again soon?] 

[Dean: u bet your sweet ass I do. im free whenever]

[Cas: You want to come to my apartment tonight? We can watch a movie or something and order in.]

[Dean: u had me at going to your apartment, m & c are driving me crazy. I'll be there @ 8] 

~

They decide to watch Zootopia, at Cas’s insistence. Dean scoffs at having to watch a cartoon, but Cas knows he's made the right decision when Nick is introduced. 

“Dude. I never thought I'd say I identify with a cartoon fox,” he says, shaking his head and laughing when Nick justifies hustling people to Judy. Cas smirks, satisfied, and takes a swig of his beer. 

As the movie progresses, Dean gets more and more into it. By the end, he’s downright emotional. “Now _that_ is a solid friendship. He heard her out and decided to forgive her. Forgiveness… it doesn’t always come that easy.” 

Cas turns to him, setting his beer on the coffee table. “You say that like you have firsthand experience.” 

“Well, most people do, right? Even for little things, someone always fucks up and people have to decide whether to forgive or hold it against them. It’s hard. Especially when it comes from someone you care about, you know?” Dean shakes his head, eyes glued to the screen. “I’m not so sure Nick and I are the same. But I wish we were.” 

Deciding to leave that story for another day, if at all, Cas turns back to the TV. They finish the movie in silence, Cas zoning in and out, deep in thought. What makes Dean so unsure of himself? Castiel obviously hasn’t known Dean for long, so he can’t necessarily have an opinion, but Dean seems like a good man. The fact that he took one for the team and watched a children’s movie he ended up really enjoying says a lot to Cas. 

It also hasn’t escaped his notice that neither of them have made a move. Which seems odd, because both of them had insinuated they wanted to have sex again. This, the movie watching and sharing semi-private information, seems more like the budding of a new friendship, something Cas is a little weary of, considering how sexually attracted he is to Dean. 

“You in there, Cas? You’ve been zoning out for like five solid minutes.” 

“Hmm?” Castiel looks around and Dean is up and setting the TV remote on the coffee table, roaming around the living room to look at the bookshelves. “Ah, yeah, I have a lot of books.” 

Dean reaches forward to pick out one of them. “The Pendragon series? Sammy loved these growing up.” 

“Is Sammy your brother?” 

“Yeah,” Dean says, smiling, “he’s still in high school, but the squirt is gonna do some incredible things.”

It’s quiet without the TV on, and it’s making Cas nervous. He stands and stretches his arms above his head. “You two are close?” 

“We fight sometimes, but I’d do anything for him. You got any siblings?” 

Cas approaches Dean and stares at the book in his hand. “Two brothers. Jimmy and Gabriel.” 

“Older? Younger?” 

“Gabriel is three years older. Jimmy is my twin.” 

Dean almost drops the book he’s holding and Cas finally looks up to meet his eyes. They’re incredulous. “There are two of you? God, that’s dangerous.” 

Laughing, Cas grabs the book out of Dean’s hand. “We’re very different. He went to school for biblical studies and hopes to be a preacher someday. Hell, he's engaged.” 

He and Jimmy had always gotten along, but he isn't kidding when he says they're different. Cas grew up to be a bit of a troublemaker, and willing to try out everything life has to offer. Jimmy knows what he wants, always has. 

Dean looks surprised, but takes it in stride. “That must have been interesting growing up. What's Gabriel like?” 

“He's even more of an oddball than I am. He's never gotten in any legal trouble, but he has a tendency to be a dick and make his life difficult. You'd like him, I bet.” 

Dean grins and Castiel feels something inside of him click into place. It's like looking at Dean smile, watching him look through his bookshelf, seeing how comfortable the man is in Cas’ living room - 

He's developing _feelings_ for the guy. Mushy, red-hearted, stay-the-night feelings. Goddamn it. That feeling of unease from earlier is the next wave of unwanted emotion and he wishes someone would put him out of his misery. 

“Hey, are you okay?” Dean reaches forward to lay his hand on Castiel’s forearm, sincere concern in his eyes, and Castiel is lost. 

He steps forward and runs a hand up Dean’s bicep, across his shoulder, and finally delves his fingers into his soft hair. There isn't much of it in the back but it makes it easier to scratch lightly at his scalp, and Dean closes his eyes, exhaling shakily. Cas leans forward and ghosts his lips across Dean’s jaw and Dean reaches for his hips and squeezes gently. His right hand slides to Castiel’s back, stroking gently and Cas presses an open kiss to his throat. 

This quiet exploration is so much different than the frenzy from the night before and Cas doesn't know what to make of it. He lowers his head a little to nip at Dean’s collarbone and hears a soft moan. They push closer simultaneously and Cas lifts his mouth to Dean’s. 

This kiss is just as slow, steady, as everything else they've done in the past few minutes and it's starting to make Cas itch. Relationships are messy. His last one ended so badly he swore he'd not get into another one until after he graduated college. He's really good at compartmentalizing - sex is sex and anything deeper than that is off limits. But this kiss is dangerously easy and it scares him so he does the one thing he can to dive back into safe territory. 

“Hey,” Cas says, nibbling at Dean’s earlobe for a second before continuing, “You want to continue our… experiment?” 

Dean leans back and for a second, Cas sees something that looks like disappointment in his eyes. Before he can say anything, Dean surges forward and all thought of logic is lost in the sensation of their lips sliding together, mouths pushing and opening and tongues crashing, chaotic. Cas moans and they make their way back to the couch, unwilling to separate. Dean climbs onto Castiel’s lap, wasting no time in grinding their hips together. They pull away from one another and groan, Cas settling his hands on his ass and lifting his hips to meet Dean’s. 

Dean runs his tongue lightly down Cas’s throat, pausing to moan as the rhythm they've built becomes frantic. All Cas wants is to take their jeans off, even just the two layers of denim gone would make all the difference and he's reaching for Dean’s belt buckle when a cell phone goes off. 

Dean freezes and groans in frustration, pulls it out of his back pocket and gives Cas a mumbled, “Sorry,” before answering. 

“Yeah?” The expression on Dean’s face goes from annoyed and aroused to panicked in 2.5 seconds. “What?! Are you guys okay?” A pause. Dean closes his eyes and sighs, frustrated. “Okay. I'll be home in like 10 minutes.” 

“What's going on?” 

He leans down and rests his forehead on Cas’s, breathing hard. “I want to finish this, believe me, but I have to go.” He eases off of Cas and Cas is still so hard it's painful. 

Dean walks away to put his shoes and coat back on. “Meg and Charlie set the kitchen on fire. They said there isn’t much damage but they're both pretty shaken up and don't know how it happened, so I'm going to go check it out.” 

The door is already open and Dean is slipping out of it when Cas grabs a hold of Dean’s arm. “Do you want me to come with?” 

Dean first looks at Castiel’s hand on his arm and then up at his face. “No, that's alright.” He pats Cas’s hand and then squeezes it before letting go. “See ya later, Cas.”

Cas locks the door behind Dean and bolts to the bathroom, peeling off his clothes and starting the shower. That was… how does everything Dean does make him feel like he was 12 and masturbating for the first time? He'd nearly come in his pants after 45 seconds of rutting on the man, _fully clothed_. 

He relives that experience in vivid detail as he jacks off in the shower, Dean’s name on his lips as he comes. He stands under the scalding water for much longer than he needs to, thinking about what this thing with Dean is becoming and what he _wants_ it to become. 

Castiel has always been a big believer in going with the flow. If it happens, it happens. Que sera, sera and all that jazz. Maybe it's time to let go of his hang-ups about relationships and just see what happens. 

Then again, maybe he can drink beer and watch _Bob’s Burgers_ and forget about everything else for as long as it takes for him to stop acting like an idiot with a crush. Yeah. That sounds better.


	4. Reach Out

**Notes for the Chapter:**

> Mary is in this chapter, and I haven't caught up on season 12 yet, so her characterization is probably off. Just assume it's the same Mary we've always seen in fic.

The damage _was_ minimal. He’ll give them that. What Dean won’t give them is the satisfaction of knowing they’d interrupted something. 

“You were at Cas’s place, right?” Charlie asks, handing Dean a flashlight so he can take a closer look under the burners. 

“When did we clean these last?” Dean can hear Charlie groan in aggravation as he dodges another question. 

“Uh,” Meg says, “have we ever cleaned them? I didn’t even know you could lift up the whole stovetop to clean underneath, honestly.” 

Dean looks up at the ceiling and breathes out, slowly. It’s not their fault entirely - he’d never cleaned them, either, and he knows better. Really, there’s no reason for him to be in such a foul mood. Except the weirdness that went down at Castiel’s apartment. And being interrupted before it could go any farther. Yeah, he’s definitely mad about the lack of sex currently happening. 

They work together to clean all of the burners thoroughly, Meg talking about something that has to do with her classes and Dean saying nothing at all. Anxiety about the whole situation is settling right under Dean’s skin, irritating and impossible to ignore. His phone beeps with a message and he stops cleaning to check it. 

[Cas: Hey, is everything alright? I'm a little worried the house burnt down or something.]

[Dean: Nah, everything is fine, it was just something in the burner.]

He puts his phone away before Castiel can text him back and closes his eyes. When he opens them, Charlie is staring at him with concern. 

“Dean,” she says, “what's -” 

“I'm fine,” he snaps. Dean runs a hand through his hair and sighs. “Sorry. I'm just not in the mood to talk. I'm gonna hit the hay.” The girls let him go and Dean heads to his bedroom, trying really hard not to think about anything at all as he undresses and climbs into bed. It's barely 11pm but the only thing he can think to do to shut his brain off is to sleep. So he does. 

Monday is no better, but he's at least begun to work through some of the things swirling around his thoughts. Like how gentle that first kiss had been between he and Cas the night before, or how nice it had been to just kick back and watch a movie with the guy, or how he didn't know how his father would react to Dean being into dudes if he were alive. 

That last thought hurts more than he's willing to admit to himself. After four hours of moping around the house and debating what to do and absolutely not waiting for a text from Cas, he decides he needs to talk to his mom. 

As soon as he decides, he marvels at what a great idea it is - the three hour drive will be rejuvenating, he's always thought there's nothing like a long drive to clear the mind. Dean tells Meg and Charlie he'll be back in a couple of days and heads out, not even bothering to pack a bag because he still has some clothes and toiletries at home. He turns his phone off and shoves it in his pocket, vowing not to turn it on until he gets his shit together. 

The drive is just what Dean needs. Windows rolled down, just-barely-warm air hitting his face and his music turned up loud. If he throws on an Outfield tape, still in the car from his brother’s brief 80’s pop phase, well, no one needs to know. He feels so much better by the time he arrives home, he wonders if maybe he was overreacting by making the drive home to talk about his feelings. 

It’s past 6 in the evening so both Sam and his mom are probably home. He unlocks the front door and walks in the house, smelling something delicious coming from the kitchen. “Mom? Sammy?” 

Mary runs out of the kitchen, surprise and worry and glee written all over her face at once. “Dean! What are you doing home, I thought you’d decided to stay at school over break? Is something wrong?” 

Dean comes forward and gives her a hug, chuckling. “What, I can’t surprise you guys every once in awhile? It’s gotta be way too quiet with nerd boy just reading all the time.” 

“Nerd boy. Good one, I’m sure he’s never heard that before.” Mary rolls her eyes and makes her way back into the kitchen. “Actually, Sam is out with some friends to see a movie tonight.” 

“On a school night?” 

“It’s 6:30 and he’s almost 17. I think he can handle being out past dark. You’re worse than your father was.” 

Dean freezes and stares at the old linoleum floor, scrutinizing how it starts to curl up where it meets the bottom of the cabinets. Sighing, Mary comes over and puts her arm around Dean’s shoulders. “What is it, Dean?”

“I, uh,” Dean stops to clear his throat, “I had a question. About Dad.”

Mary looks confused. Dean can't blame her, honestly, Dean hadn't talked much about John since he'd died four years previously. To bring him up now is hard, but he has to do it. 

“What were his political views on social issues?” 

Now Mary’s eyebrows fly way up, and she pulls her arm back to put her hands on her hips. “What?” 

“Just… can you tell me?” 

“Dean, he was pretty absorbed in his work. He didn't talk a whole lot about politics, and I know he didn't vote. I'm going to finish dinner while you work up the nerve to ask what you really want to know about.” With that, she turns back to the stove, stirring what looks like simmering spaghetti sauce. Dean huffs in frustration, but says nothing for a while. 

They eat dinner like nothing happened, Dean asking about how work is going for his mom and how school is going for Sam, and Mary asking about Dean’s college life. He mostly talks about Meg and Charlie and their antics, not much else. 

At 8 o'clock, Dean realizes he's running out of time. He wants to ask Mary before Sam comes home and looks at him with those puppy dog eyes and tries to talk about feelings. At least his mom will probably be no-nonsense about it. 

“So, I'm kind of seeing someone.”

Mary glances at him over her shoulder, elbow-deep in dirty dishes. Dean grabs a hand towel and starts drying off the clean ones. “Yeah? Do I really want to know what ‘kind of seeing someone’ means?” 

“Probably not.” He pauses and places a plate on the drying rack. Like a bandaid, just get it over with. “His name is Castiel.”

Mary stops mid-swipe while scrubbing off a dish, turns to Dean, and stares. He stares down back, gulping nervously, thinking he should have said that more tactfully or something, anything to break this horrible tensio-

“What kind of name is Castiel? Poor kid probably had a horrible time in elementary school.”

Dean flounders for a second before laughing, feeling all of the tension bleed from his pores at once. “He goes by Cas, which probably helped.”

“How did you two meet?”

“Meg invited him over.” No way is he going to tell his mother that Cas was an experiment gone way too right. 

“It worries me that you two met through Meg of all people,” she grimaces, “but if you're happy, I'm happy.” 

Dean sets the hand towel down and turns, crossing his arms and resting his hip on the edge of the sink. “Thanks, Mom.” He worries his bottom lip with his teeth and Mary sighs. 

“Dean, your father would have come around. He was… a traditional guy. He wanted you boys to have it all some day - the picket fence, the wife, the kids, the apple pie life.”

“I can have that with a guy.”

“He died before marriage was even possible between two men here.” They both turn as a car pulls into the driveway, the gravel crackling like popcorn. Mary places her hands on Dean’s shoulders. “The truth is, Dean, we have no way of knowing how he would have reacted. But I do know that, even if it had been bad, he would have gotten over it. Because he loved you.” 

Dean nods and pulls Mary in for a hug. Sam opens the front door and Dean grins, pulling back from his mom and rushing over to give his little brother a hug. 

“Dean!” Sam exclaims, clapping him on the back. “What are you doing home, I thought you were staying at school over break?” 

“I got bored.” Dean shrugs. “Thought it'd be nice to have a home-cooked meal.”

Sam rolls his eyes. “Whatever, you missed us.”

“Yeah. I guess I did.”

~

Dean leaves his family the next morning. He and Sam had stayed up late playing video games, to Mary’s dismay - Sam still had school the next day. It was good for Dean to get away, even if just for a day. The drive back is just as relaxing, except this time he doesn't attempt to keep his mind blank. He thinks about Cas, about what he wants. 

Dean wants to get to know him better as a person. He wants to see if he talks during movies at the theater. He wants to know if he puts milk or cereal in the bowl first. He wants to know what his parents are like, how they influenced him growing up. 

Similarly, Dean wants to get to know him better physically as well. He wants to know where he’s ticklish. He wants to know if he prefers to top or bottom. He wants to know what the fine hairs on Cas’s thighs feel like against his cheek. 

There are a couple of options to consider: Dean could ask Castiel out on a date. He could potentially ask him to be in an exclusive relationship as a result of said date. He has a feeling Cas would consider the idea of an open relationship, but that doesn't appeal to Dean. They could get into a friends with benefits deal, but again, Dean just has a feeling that wouldn't work out on his end. There's something about Cas that makes him want to do irrational things, like buy him a bong just to see if it would make him smile in that cute and flirty way of his. The idea of sharing that smile with anyone else makes Dean’s stomach hurt, and _that_ is when he realizes that he's definitely, 100%, bonafide gay for Cas. 

“That's stupid, you can't just be gay for someone,” he mutters aloud to himself, turning the car onto the road to his house. Meg had been right; he was homoromantic and bisexual. He rolled the words around in his mind, feeling them out. It felt weird to think of the words and attempt to fuse them with the image he has created in his mind for himself. 

Before he can think too hard, he pulls into the driveway and sees Charlie on the porch swing, reading a book. He climbs out of his car and Charlie looks up and waves. 

“Didn't expect you back so soon.” Dean hops up onto the porch and sits next to his friend. 

“Yeah, well.” He rubs the back of his neck, debating whether or not to spill the beans to Charlie about his self-discovery. “Where’s Meg?” 

“I think she’s at Cas’s place, actually. He was over here earlier and she went home with him to watch a movie or something, get out of the house for a bit.” 

Dean plants his feet to halt the swing’s motions. “Cas was here?” 

Puzzled, Charlie tilts her head at him. “Yeah. Dean, have you checked your phone?” 

“My…,” he takes his phone out of his back pocket. “No. It’s been off since I left yesterday.” 

Charlie closes her book and hops up from the swing. “You should really check it.” 

Dean stares down at his phone, imagining the absolute worst. That he’d crossed a line during their movie night, that Cas was actually seeing someone else, that he’d accidentally seen a pair of Dean’s pink panties in his bedroom that first night and it was a deal-breaker. The last one was less plausible, but just as horrifying to Dean, for more than one reason. No, he can’t do it, he can’t turn his phone on and just _check_ , he has to go over to Cas’s place and tell him how he feels. 

Jumping off the porch and running to his car, he tries not to think about how he’s never done anything like this before and has no way of knowing if he’s doing it the right way. Oh well. Now or never.


	5. Since You've Been Gone

**Notes for the Chapter:**

> I signed up for 2 different fic challenges right after I posted the last chapter (in February, yikes, sorry!), so I've been frantic between that and getting a new job. So, finally, here's another chapter! I promise I didn't give up on this story! Thanks for all your kind comments and kudos :)

The glow of the cell phone is the only thing lighting up the room, but Castiel doesn't have the heart to get up and turn on a light so his eyes don't hurt from the brightness. He's been typing and retyping this text message for over 30 minutes, trying to find the best way to say what he wants without sounding like a total moron. 

[Cas: Hey, Dean, listen I think you're great and]

[Cas: I don't know how you feel, but I just wanted to let you know that I]

[Cas: I don't want to be your experiment anymore so we should]

Finally, after a few more attempts and one terrifying moment when he drops his phone on his face and almost hits “send” accidentally, Cas sends a text on purpose. 

[Cas: I've been trying to figure out a way to say this for an hour, but I'll just say it: would you be interested in going on a date with me?] 

There. Simple, to the point. Probably didn't need that bit at the beginning, but whatever, it's done. He locks his phone and sets it on the bedside table, not really expecting a reply at 2am on a Tuesday. Cas isn't sure if Dean works during the week or not, but figures even if he doesn’t, there isn't much reason to be up this late in the middle of the week. 

The decision to make a move had not been an easy one to make. Between needing to resolve his feelings and do _something_ and staring into the mirror and saying to himself, “You're being way too dramatic about this, you met the man 3 days ago,” he's had a stressful Monday. And he hadn't texted Dean, nor had Dean texted him. So, like most sketchy decisions, this one was made in the wee hours of the morning. 

It isn't even particularly risky. He's not declaring his love or even asking for them to be exclusive. Really, asking for a date is just asking to get to know someone better - with the possibility of making out at the end of the night. Or sex. Cas could roll with either. 

He falls asleep with his phone clutched in his left hand, anticipating the vibration of an incoming text. 

~

The text never comes. 

Bright sunlight blasts through the window and onto Cas’s face, disrupting his sleep. He glances at his phone and sees it's almost noon. No message from Dean. 

Groaning, he rolls out of bed and gets ready for the day, though he has no idea what he's going to do. After some deliberation, Cas decides to go for a run. It's a cloudless, sunny day and there are hardly any people out on the residential road. After a couple of miles, he realizes he’s on Dean’s road. Rather than turning back, he just hopes Dean isn't out on the porch. 

Dean isn't, but Meg and Charlie are, and they call to him, prompting him to take out his headphones and wave up at them from the road. 

“Cas! Come up here, we gotta talk to you about something.” 

He hesitates. “Is Dean home?” 

Meg scowls, flicking a cigarette into the bushes and ignoring Charlie’s indignant, “At least use the ashtray!” 

“No, that's what we need to talk to you about.”

“O...kay.” Cas jogs up to the porch and Charlie pats the space on the swing next to her. Meg turns at her spot to face the two of them. 

“Dean left yesterday afternoon to go see his mom. He said he'd be back in a couple of days, which I get it, he needs to visit with his family, but we’re concerned because he started acting funny after he came back from your apartment on Sunday.” 

Cas wrinkles his eyebrows in confusion. Thinking back on the night he'd come over for movies, there wasn't anything that stood out to Cas as something that would warrant an emergency visit home. “I don't…”

Charlie pats his knee affectionately. “Did anything happen?” 

“Um.” Cas lets out a deep breath. “We watched Zootopia and then we made out and then you guys called about the kitchen and he left.” That wasn't entirely everything, though. “He did mention something cryptic about forgiveness? But I didn't ask him to go into detail about it.”

Both of the girls lean back and nod at that admission. It's quiet for a moment, the breeze moving the tree branches being the only thing to break the silence. Castiel takes another deep breath, steeling himself. “Have either of you spoken with Dean today, via text or phone call?” 

Meg tilts her head. “That's a very specific inquiry, Clarence.”

Blood rushes to Cas’s face, giving him away. He isn’t usually a blusher. Damn it. “I texted him late last night and he hasn't responded.” The girls stay quiet, and he's forced to continue. “I asked him out on a date.”

Meg looks positively shocked, but Charlie just looks excited. “That’s great, Cas!” 

“Great? Did you miss the part where I said he hasn’t responded?” Neither answers, because what could they really say to that? It's possible Dean’s phone is dead or he's busy with his family and doesn't have time to reply, but it's also entirely possible that Cas has made him uncomfortable. He wants so badly to take it back, he can feel the urge to send a text to fix it building just under his fingertips. 

He lets it go. At the very least, perhaps he can talk to Dean when he gets home, let him know that it's not a big deal and they can just forget Cas ever said anything. Yeah, he can do that. It's not like he's head over heels for the guy - thank god - but he does want to get to know him better while also having more sex and making out a lot. 

Cas announces he's going home and Meg asks if she can join him, to get out of the house for a while. He asks Charlie if she wants to join but she decides to stay behind in case Dean gets back. They walk the twenty minutes or so to Castiel’s apartment, neither of them saying much of anything. Cas figures this is as good a time as any to ask Meg what he's been wondering about for a few days. 

“So how long have you and Charlie been together?” 

Meg shakes her head, smiling ruefully. “It's been four days since you came over for the first time. How did you pick up on something that Dean hasn't figured out and he lives with us?” 

“It's not that hard. You two are like a well-oiled machine. And also that thing Charlie said about there not being a romantic breakfast for two in the house - for Dean, anyway.”

“Sneaky.” They walk a few paces in silence and Cas worries he’s overstepped. He’s about to apologize and change the subject when she goes on, “It’s been a while.” 

“Why haven't you guys told Dean?”

“Because,” she chuckles, “he's allergic to feelings and he'd ask a lot of questions and…,” her laughter dies, “I can be a real asshole sometimes. I’m afraid he’ll think Charlie deserves better.” 

Silence falls between the two of them again and Cas doesn’t know what to say. He doesn't have a good solution or word of advice for Meg and Charlie’s issues, so he doesn't offer any. 

With the two of them subdued and lost in their own thoughts, the idea of doing anything productive when they get to Castiel’s apartment isn't favorable. So Meg opens Netflix on his TV and turns on Clueless, which they watch in comfortable silence. 

Halfway through the movie, they hear a car pull into the parking lot and Meg scrambles forward to pause it. “That's Dean’s car.” 

“What??” Cas jumps up and peers through the blinds. Sure enough, there’s Dean, climbing out of his ‘67 Impala and practically jogging towards the stairs that lead to the apartment. Cas stares at Meg, anxiety clear in his eyes, and she just lifts an eyebrow as Dean knocks on the door.

She strides over to unlock the door and Dean catches himself before he starts talking, glancing around Meg to catch Castiel’s eye. “I'm just going to… get out of your hair. I have to take care of something.” Giving the two men a salute, she squeezes out past Dean. Cas endures a few moments of blind panic and as Dean steps into the apartment and closes the door behind him, he decides to play it cool. He shoves his hands in his pants pockets. 

“Hello, Dean.” He holds back a wince; too formal, he should have said ‘hi’ instead. “What’s, uh… what’s up?” So much for playing it cool. 

Dean looks frazzled, and he doesn’t look up at Cas’s face as the words just start spilling from his mouth. “Look, I’m bad with emotions. That’s not a secret to anybody. But you… make me feel them. Emotions, I mean.” He runs a hand through his hair, frustrated. “I don’t know what I’m doing, but whatever it is, I kinda want to do it with you. I just, um. Wanted to know if you want to go on a date with me. Sometime.” 

After Dean’s finished, still looking down at his shoes, Cas is equal parts confused and elated. “Dean… did you read the text I sent you last night?” 

Dean’s head whips up. He frowns. “Oh, uh, no. My phone has been off since yesterday morning.” Pulling the phone out of his pocket, he turns it on and they wait, standing awkwardly in silence as it boots up. Dean looks up a couple of times, expecting Cas to say something probably, but Castiel just stares at the phone and waits. He almost starts laughing just to break the tension. Finally, it loads and Dean clicks through his messages. It’s unbearable to wait, but Cas does, only stepping closer as he reads it. 

Everything seems to be happening in slow motion for Cas. The time it takes Dean’s face to go from scowling confusion to complete wonder feels like minutes. When Dean looks up at Cas, a question forming behind his lips, Cas surges forward and crashes their lips together, a little harder than he meant to. Their teeth clack and Dean chuckles, pulling back slightly to take some pressure off and lead the kiss in a better direction. Castiel follows, moaning in the back of his throat softly when their tongues slide together. 

Cas pushes Dean forward against the front door, and it’s perfect. The kiss, the hands gently tugging on his hair, the soft noises coming from Dean. He never wants it to end. 

Unfortunately, after a few minutes and the beginnings of a boner in his pants, Dean pulls back. “As much as I’d love to continue this… I’m serious. I want to go on a date.” 

“Okay, yeah,” Cas says breathlessly, running his fingers along the back of Dean’s neck. Dean shudders and his eyelids flutter. 

“I mean, I kinda want to do this… differently. Than we’ve been doing, I mean. I, uh, I just wanna get to know you before we take things further. Again.” 

Flustered Dean is so adorable, it’s hard for Cas to not lean in for another kiss. He smiles. “I’m actually honored. No one’s ever requested the whole traditional route before. It’s refreshing.” Cas leans in to nuzzle his nose next to Dean’s ear before leaning in to whisper, “And it’ll make the next time we _are_ in bed that much more exciting.” 

Dean gulps and his neck flushes red, but he smirks. “I can’t believe you’re actually willing to have sex with me again after the disaster from last time.” 

Cas tilts his head back and laughs. As far as first times go, his with Dean was extremely memorable, not just because he was kneed in the balls - which, yeah, _ouch_ \- but he’s never been with anyone who could have a conversation about 80s music one minute and then give a successful first blowjob the next. He shakes his head, running his nose along Dean’s throat in the process. “Dean, you were fantastic. And, if you want there to be a next time, I’m sure you’ll be much less nervous. Especially after our date, when we know each other better.” 

They kiss for a little while longer until Dean pulls away and unwinds his fingers from Castiel’s hair. “Okay, I’m going to go before my resolve breaks. When are you free, Cas?” 

“I’m a free man all week.” 

Dean grins, and the sight nearly made Castiel’s heart melt. When did he become such a softy for a cute guy with a dazzling smile? “Cool, how about tomorrow, then? I could pick you up at 6.” 

Unable to resist, Cas leans forward to give Dean a quick kiss on the lips before he backs out of the doorway. “Sounds perfect. Where are we going?” 

“It’s a surprise!”

Normally, Castiel hates surprises. But every second with Dean has been a pleasant surprise and he has no doubt that whatever Dean picks will be fine. When he closes his door - after one more kiss - he finds himself more excited about a date than he can ever remember feeling.


End file.
